Optoelectronic component, organic functional layer, and method for producing an optoelectronic component

ABSTRACT

An optoelectronic component includes a substrate, a first electrode, a second electrode, and at least one organic functional layer, which is arranged between the first electrode and the second electrode. The organic functional layer includes a matrix material, a first compound, and a second compound. The first compound interacts with the second compound, and the first compound and/or the second compound interacts with the matrix material. A conductivity of the organic functional layer is produced by the interactions.

This patent application is a national phase filing under section 371 ofPCT/EP2014/063410, filed Jun. 25, 2014, which claims the priority ofGerman patent application 10 2013 106 949.5, filed Jul. 2, 2013, each ofwhich is incorporated herein by reference in its entirety.

TECHNICAL FIELD

The present invention relates to an optoelectronic component, to anorganic functional layer, and to a method for producing anoptoelectronic component.

SUMMARY

A problem frequently affecting components which emit radiation, such asorganic light-emitting diodes (OLEDs), for example, is that of providingone or more layers having a high conductivity of electrons and/or holes.A higher conductivity in the layers, such as in hole transport orelectron transport layers, for example, often positively influences theexciton density in a layer which emits radiation. In the event ofinadequate conductivity in the layers, in contrast, increased efficiencylosses and luminance losses in components that emit radiation may be theconsequence.

Embodiments of the invention specify an optoelectronic component, anorganic functional layer which can be used therein, for example, andalso a method for producing an optoelectronic component, exhibitingimproved conductivity.

BRIEF DESCRIPTION OF THE DRAWINGS

For a more complete understanding of the present invention, and theadvantages thereof, reference is now made to the following descriptionstaken in conjunction with the accompanying drawings, in which:

FIG. 1 shows the schematic side view of an optoelectronic component,

FIG. 2 shows the concentration dependence of the specific conductivity Kof comparative examples and according to an inventive embodiment,

FIG. 3 shows the measuring geometry of an organic test structure,

FIG. 4 shows the specific conductivity K by interaction of a firstcompound and a second compound, according to a further embodiment, incomparison to comparative examples.

In the working examples and figures, constituents which are identical orof identical effect are each provided with the same reference symbols.The elements shown and their size relationships with one another shouldbe considered in principle not to be true to scale. Moreover, identicalworking examples of first and second compounds and matrix material aregiven the same abbreviated designations.

DETAILED DESCRIPTION OF ILLUSTRATIVE EMBODIMENTS

In the text below, advantages and advantageous embodiments anddevelopment of the subject matter of the invention will be in moredetail using figures and working examples.

An optoelectronic component according to one embodiment comprises asubstrate, a first electrode, a second electrode, and at least oneorganic functional layer which is arranged between first electrode andsecond electrode. The organic functional layer comprises a matrixmaterial, a first compound and a second compound, the first compoundinteracting with the second compound, and the first compound and/or thesecond compound interacting with the matrix material. The interactionsgenerate a conductivity in the organic functional layer that is improvedrelative to the conductivity of the matrix material alone.

The inventors have surprisingly determined that in the operation of anoptoelectronic component, a combination of matrix material, firstcompound and second compound in at least one organic functional layerbrings about increased conductivity in the organic functional layer.This results, furthermore, in an increased luminance and recombinationefficiency, and so leads to an increased luminous efficiency of theoptoelectronic component. The electromagnetic radiation generated bycharge carrier recombination can in principle be outcoupled through thefirst or second electrode or through both.

Electromagnetic radiation here and below preferably compriseselectromagnetic radiation having one or more wavelengths or wavelengthranges from an ultraviolet to infrared spectral range, theelectromagnetic radiation more preferably being visible light havingwavelengths or wavelength ranges from a visible spectral range betweenabout 350 nm and about 800 nm.

In the context of this specification, the term “component” comprehendsnot only completed components such as, for example, organiclight-emitting diodes (OLEDs) but also substrates and/or organic layersequences. An assembly of an organic layer sequence with a firstelectrode and a second electrode may already constitute a component, forexample, and may form a constituent of a superordinate second component,in which, for example, electrical connections are additionally present.

“Arranged between first electrode and second electrode” does not ruleout the arrangement between the electrodes of further layers orelements, although the functional organic layer is always at least inindirect electrical and/or mechanical contact with one of theelectrodes.

“Conductivity” here and below refers to the capacity of at least onesubstance to transport charge carriers—for example, negative chargecarriers (electrons) and/or positive charge carriers (holes). Theconductivity may be generated by interaction of at least two or threesubstances, as for example, by interaction of the first compound withthe second compound, or of the first compound and/or of the secondcompound with the matrix material. The conductivity is dependent on theproduct of charge, charge carrier concentration and mobility of thecharge carriers.

According to one embodiment, the conductivity of the organic functionallayer is greater than a sum of a first conductivity, generated by soleinteraction of the first compound with the matrix material, and of asecond conductivity, generated by sole interaction of the secondcompound with the matrix material. The interaction of first and secondcompounds generates increased particle transport, holes, for example, inthe organic functional layer, and an increased luminance and efficiencyin the optoelectronic component.

“Sole interaction” in this context means that first compound and matrixmaterial or second compound and matrix material interact exclusivelywith one another. More particularly “sole interaction” may mean thatonly first compound and matrix material or second compound and matrixmaterial are conductive.

The interaction of the first compound with the second compound and/or ofthe first compound and/or of the second compound with the matrixmaterial means in this context that between-molecule forces,intermolecular forces, intramolecular forces and/or chemical bonds areformed between the first compound and the second compound and/or betweenthe first compound and/or second compound and the matrix material,examples being ionic interaction, hydrogen bonds, dipole interaction,Van der Waals interaction, ionic bonding, covalent bonding, coordinatebonding and/or metallic bonding.

In particular, at least one coordinate bond is formed by the firstcompound with the second compound and by the first compound with thematrix material and/or by the second compound with the matrix material.

“Coordinate bond” here and below indicates that between an electrondonor and an electron acceptor a bond is formed, the electron donorproviding all the electrons required for the formation of the coordinatebond, and the electron acceptor accepting the electrons provided. Inparticular, the electron donor and/or the electron acceptor may exchangeelectrons only partly or to a slight extent.

According to one embodiment, the first compound is an electron acceptorin relation to the matrix material and/or an electron acceptor inrelation to the second compound.

According to a further embodiment, the second compound is an electronacceptor in relation to the matrix material and/or an electron donor inrelation to the first compound.

According to another embodiment, the second compound in comparison tothe first compound is more strongly electron-accepting relative to thematrix material.

According to one embodiment, in addition to first and second compounds,there may also be additional compounds—for example, one to threeadditional compounds—embedded in the matrix material, and being capableof interacting with the first compound, the second compound, the matrixmaterial and/or one another, by forming coordinate bonds, for example.Alternatively or additionally the matrix material may be a mixture oftwo or more different matrix materials.

According to one embodiment, the optoelectronic component is an organicelectronic component and is formed, for example, as an organiclight-emitting diode (OLED). This OLED may have a first electrode on thesubstrate, for example. Applied over the first electrode there may be atleast the organic functional layer, or a plurality of functional layerscomprising organic materials. Applied over the organic functional layeror the plurality of functional layers is a second electrode.

The organic functional layer here may be selected from a group whichcomprises a layer that emits radiation, a hole transport layer, a holeinjection layer, and a hole blocking layer. More particularly theorganic functional layer is a hole transport layer and/or hole injectionlayer.

Any further organic functional layer may be selected from a group whichcomprises an electron injection layer, an electron transport layer, ahole blocking layer, or a layer which emits radiation. The layer whichemits radiation may comprise a single layer or a plurality of sublayers,examples being layers or sublayers which emit in the green, red and/orblue spectral range of electromagnetic radiation. Alternatively oradditionally it is possible for the electron injection layer, electrontransport layer and hole blocking layer to feature an individual layeror a plurality of sublayers.

The layer which emits radiation may also have an active region which issuitable for giving off electromagnetic radiation in the operation ofthe organic electronic component.

According to one embodiment, the optoelectronic component mayadditionally have an encapsulation.

Alternatively, according to one further embodiment, the optoelectroniccomponent is formed in the form of a transistor, a field effecttransistor, for example, or a solar cell or a photodetector.

The substrate may comprise glass, quartz, polymeric films, metal, metalfoils, silicon wafers, or another suitable substrate material. The OLEDmay also be designed as a “bottom emitter”, meaning that theelectromagnetic radiation generated in the active region is given offthrough the substrate. In that case the substrate has transparency forat least part of the electromagnetic radiation. Advantageously, thefirst electrode, which may be designed as anode, may be transparentand/or comprise a material which injects holes. The first electrode mayhave or consist of a transparent conductive oxide, for example.Transparent conductive oxides (“TCO”, for short) are generally metaloxides, such as zinc oxide, tin oxide, cadmium oxide, titanium oxide,indium oxide or indium tin oxide (ITO), for example. The group of theTCOs includes not only binary metal-oxygen compounds, such as ZnO, SnO₂or In₂O₃, for example, but also ternary metal-oxygen compounds, such asZn₂SnO₄, CdSnO₃, ZnSnO₃, MgIn₂O₄, GaInO₃, Zn₂In₂O₅ or In₄Sn₃O₁₂, forexample, or mixtures of different transparent conductive oxides. TheseTCOs do not necessarily conform to a stoichiometric composition, and mayalso be p- or n-doped.

The at least one organic functional layer may feature organic polymers,organic oligomers, organic monomers, organic small nonpolymericmolecules (“small molecules”) or combinations thereof.

The second electrode may be designed as cathode and may therefore serveas a material which injects electrons. As cathode material, amongothers, in particular aluminum, barium, indium, silver, gold, magnesium,calcium or lithium, and also compounds, combinations and alloys thereof,may prove advantageous. Alternatively or additionally, the secondelectrode may also have one of the abovementioned TCOs. Additionally oralternatively, the second electrode may also be of transparent designand/or the first electrode may be designed as cathode and the secondelectrode as anode. This means in particular that the OLED may also bedesigned as a “top emitter”.

The first and/or the second electrode may each be of extensive format.Consequently, in the case of an OLED, it may be made possible for theelectromagnetic radiation generated in the active region to be given offextensively. “Extensive” here may mean that the organic electroniccomponent has an area of greater than or equal to several mm²,preferably greater than or equal to one cm² and more preferably greaterthan or equal to one dm². Alternatively or additionally, the firstand/or the second electrode(s) may be of structured format at least inpartial regions. As a result, it may be made possible for theelectromagnetic radiation generated in the active region to be given offin a structured way, in the form of pixels or pictograms, for instance.

In accordance with one embodiment, in the production of the functionallayer by simultaneous vaporization of the first compound, the secondcompound and the matrix material from different sources, a thirdcompound is generated by complexation of first and second compounds inthe gas phase or in the layer. In particular, the first and secondcompounds are distributed homogeneously in the matrix material.Alternatively it is possible to establish a concentration gradient offirst and second compounds in the matrix material. The third compound inparticular forms an electron donor-electron acceptor complex. Inaddition, the third compound generates higher conductivity in theorganic functional layer.

According to one embodiment, the first compound and/or the secondcompound is/are present in excess in the matrix material. By this meansit is possible to exert process control as well over the conductivity ofthe organic functional layer, through the concentration of holes, forexample.

According to a further embodiment, the matrix material is present inexcess by comparison with the first and/or second compound(s),preferably, for example, in an excess of more than 75%, especiallypreferably in an excess of above 90%. The conductivity is proportionalto the mobility of the charge carriers and to the number of chargecarriers. On addition of a first compound and/or second compound to thematrix material, there is normally a fall in mobility. However, this isovercompensated by the generation of charge carriers, and so ultimatelythe conductivity rises by several orders of magnitude. The conductivitycan therefore be controlled via the ratio of the matrix material to thefirst compound and/or second compound. Gradients horizontally andvertically are possible in terms of process technology.

The interaction of the first compound with the second compound leads tocoordination of the two compounds with one another. The organicfunctional layer therefore comprises a third compound in the coordinatedstate, in other words involving formation of at least one coordinatebond of first and second compounds. In the organic functional layerthere is a short-range order. Short-range order means that the entirelayer per se is not crystalline, but that around the first compound, inits immediate vicinity, the second compound is arranged according to aparticular pattern. The entire organic functional layer is thereforeamorphous per se, and therefore does not have any long-range order.

According to one embodiment, the first compound comprises a metalcomplex having at least one central metal atom. The central metal atomof the first compound may be selected from an element of the PeriodicSystem, as for example, from an element from transition group I,transition group VI and main group V of the Periodic System. The centralmetal atom is selected more particularly from a group which comprisesCu, Cr, Mo, and Bi.

Alternatively or additionally there may be at least two central metalatoms linked directly via a metal-metal bond and/or indirectly to oneanother. “Indirectly” in this context means that two metal atoms arebridged or linked to at least one semimetal atom and/or nonmetal atom,O, N, P, C, Si or B, for example, and no direct metal-metal bond isformed.

According to at least one embodiment, the first compound is a coppercomplex. Present in the copper complex there may be at least one coppercation in the II oxidation state.

According to at least one embodiment, the copper complex has at leastone ligand which comprises an aryloxy group and an iminium group.

According to at least one embodiment, the aryloxy group and the iminiumgroup of the ligand is a salicylaldiminate group. A salicylaldiminategroup means a ligand which is formed from a salicylaldehyde and anaromatic monoamine or diamine or an olefinic monoamine or diamine. Theligand therefore comprises an amine-fused salicylaldehyde group and iscapable of complexing between aryloxy group and the nitrogen of theiminium group, an azomethine group, for example.

According to at least one embodiment, the copper complex has one of thegeneral formulae I or II:

Formula (I) constitutes a cis isomer of the copper complex, formula (II)a trans isomer. A copper complex of this kind therefore comprises twoligands, coordinated or bonded with the copper cation.

Definitions in the formulae (I) and (II) are as follows: R₁, R_(1′),R_(2x) and R_(2x′) (wherein x is in each case a, b, c or d) are selectedindependently of one another from a group which comprises unbranched,branched, fused, cyclic, unsubstituted and substituted alkyl radicals,substituted and unsubstituted aromatics, and substituted andunsubstituted heteroaromatics. Examples of such substituents are methylgroups, ethyl groups, decahydronaphthyl groups, cyclohexyl groups andalkyl radicals, which may be wholly or partly substituted and may haveup to 20 carbon atoms. These alkyl radicals may further contain ethergroups, such as ethoxy or methoxy groups, ester groups, amide groups,carbonate groups or else halogens, especially F.

Examples of substituted or unsubstituted aromatics are phenyl, biphenyl,naphthyl, phenanthryl or benzyl.

According to at least one embodiment, R₁ and R_(1′), and R_(2x) andR_(2x′), are each identical.

According to at least one embodiment, R₁ and R_(1′) are joined to oneanother.

According to at least one embodiment, at least one of R₁, R_(1′), R_(2x)and R_(2x′) has an electron-withdrawing substituent.

According to one embodiment, the first compound comprises at least oneligand. The ligands are preferably coordinated and/or bonded to at leastone central metal atom of the first compound. Ligands may be selectedfrom a group as published in WO 2011/033023 A1 or US 2011/0089408 A1, orDE 102010013495 A1 or WO 2011/120,709 A1. An example of a suitableligand is pentafluorobenzoate, fluorinated acetate or fluorinatedacetylacetonate. A first compound may be, for example, fluorinatedcopper(I) acetate, fluorinated copper acetylacetonate or copper(II)trifluoromethanesulfonate.

The ligand of the first compound may be selected more particularly fromthe following group and combinations thereof:

fluorinated or nonfluorinated benzoic acids such as, for example,2-(trifluoromethyl)benzoic acid; 3,5-difluorobenzoic acid;3-hydroxy-2,4,6-triiodobenzoic acid; 3-fluoro-4-methylbenzoic acid;3-(trifluoromethoxy)benzoic acid; 4-(trifluoromethoxy)benzoic acid;4-chloro-2,5-difluorobenzoic acid; 2-chloro-4,5-difluorobenzoic acid;2,4,5-trifluorobenzoic acid; 2-fluorobenzoic acid; 4-fluorobenzoic acid;2,3,4-trifluorobenzoic acid; 2,3,5-trifluorobenzoic acid;2,3-difluorobenzoic acid; 2,4-bis(trifluoromethyl)benzoic acid;2,4-difluorobenzoic acid; 2,5-difluorobenzoic acid;2,6-bis(trifluoromethyl)benzoic acid; 2,6-difluorobenzoic acid;2-chloro-6-fluorobenzoic acid; 2-fluoro-4-(trifluoromethyl)benzoic acid;2-fluoro-5-(trifluoromethyl)benzoic acid;2-fluoro-6-(trifluoromethyl)benzoic acid; 3,4,5-trifluorobenzoic acid;3,4-difluorobenzoic acid; 3,5-bis(trifluoromethyl)benzoic acid;3-(trifluoromethyl)benzoic acid; 3-chloro-4-fluorobenzoic acid;3-fluoro-5-(trifluoromethyl)benzoic acid; 3-fluorobenzoic acid;4-fluoro-2-(trifluoromethyl)benzoic acid;4-fluoro-3-(trifluoromethyl)benzoic acid; 5-fluoro-2-methylbenzoic acid;2-(trifluoromethoxy)benzoic acid; 2,3,5-trichlorobenzoic acid;4-(trifluoromethyl)benzoic acid; pentafluorobenzoic acid;2,3,4,5-tetrafluorobenzoic acid;

fluorinated or nonfluorinated phenylacetic acid such as, for example,2-fluorophenylacetic acid; 3-fluorophenylacetic acid;4-fluorophenylacetic acid; 2,3-difluorophenylacetic acid;2,4-difluorophenylacetic acid; 2,6-difluorophenylacetic acid;3,4-difluorophenylacetic acid; 3,5-difluorophenylacetic acid;pentafluorophenylacetic acid; 2-chloro-6-fluorophenylacetic acid;2-chloro-3,6-difluorophenylacetic acid;3-chloro-2,6-difluorophenylacetic acid; 3-chloro-4-fluorophenylaceticacid; 5-chloro-2-fluorophenylacetic acid; 2,3,4-trifluorophenylaceticacid; 2,3,5-trifluorophenylacetic acid; 2,3,6-trifluorophenylaceticacid; 2,4,5-trifluorophenylacetic acid; 2,4,6-trifluorophenylaceticacid; 3,4,5-trifluorophenylacetic acid; 3-chloro-2-fluorophenylaceticacid; α-fluorophenylacetic acid; 4-chloro-2-fluorophenylacetic acid;2-chloro-4-fluorophenylacetic acid; α,α-difluorophenylacetic acid; ethyl2,2-difluoro-2-phenylacetate; and

fluorinated or nonfluorinated acetic acid such as, for example, methyltrifluoroacetate; allyl trifluoroacetate; ethyl trifluoroacetate;isopropyl trifluoroacetate; 2,2,2-trifluoroethyl trifluoroacetate;difluoroacetic acid; trifluoroacetic acid; methyl chlorodifluoroacetate;ethyl bromodifluoroacetate; chlorodifluoroacetic acid; ethylchlorofluoroacetate; ethyl difluoroacetate;(3-chlorophenyl)difluoroacetic acid; (3,5-difluorophenyl)difluoroaceticacid; (4-butylphenyl)difluoroacetic acid;(4-tert-butylphenyl)difluoroacetic acid;(3,4-dimethylphenyl)difluoroacetic acid;(3-chloro-4-fluorophenyl)difluoroacetic acid;(4-chlorophenyl)difluoroacetic acid; 2-biphenyl-3′,5′-difluoroaceticacid; 3-biphenyl-3′,5′-difluoroacetic acid;4-biphenyl-3′,5′-difluoroacetic acid; 2-biphenyl-3′,4′-difluoroaceticacid; 3-biphenyl-3′,4′-difluoroacetic acid;4-biphenyl-3′,4′-difluoroacetic acid; 2,2-difluoropropionic acid and/orhigher homologs thereof. If the ligands L have acidic groups, thegroups, in one preferred embodiment, may be in deprotonated form.

In at least one further embodiment, the ligand is selected from thegroup of unsubstituted, partially fluorinated or perfluorinated organiccarboxylic acids. Organic carboxylic acids may generally be selectedfrom the groups of aliphatically, saturated monocarboxylic acids;aliphatically, unsaturated monocarboxylic acids; aliphatically,saturated dicarboxylic acids; aliphatically, saturated tricarboxylicacids; aliphatically, unsaturated dicarboxylic acids; aromaticcarboxylic acids; heterocyclic carboxylic acids; aliphatically,unsaturated, cyclic monocarboxylic acids. Particularly preferred partialor perfluorinated ligands L are selected from substituted orunsubstituted compounds of acetic acid, phenylacetic acid and/or benzoicacid and are given by way of example above. Particularly preferred isunfluorinated, partially fluorinated or perfluorinated acetic acid.

According to at least one embodiment, at least one of the ligands isarranged in bridging form between two metals.

In one embodiment, a first compound has Bi as central metal atom, butthis atom is not coordinated with a bridging ligand.

According to one embodiment, the first compound, as for example, thecentral metal atom and/or the ligand of the first compound, comprises atleast one coordination site.

According to one embodiment, the first compound, as for example, thecentral metal atom of the first compound, comprises at least one freecoordination site, which is capable of accepting an electron pair of asecond substance, as for example, the second compound, and forming acoordinate bond. This may also be referred to as Lewis acid-Lewis baseinteraction.

“Coordination site” here and below denotes at least one binding site.The coordination sites of the first compound may interact with thesecond compound and/or with the matrix material. Free coordination sitesof the first compound may mean that there are empty orbitals of thecentral metal atom or of the central metal atoms, such as d-orbitals,p-orbitals or f-orbitals, for example, which are occupied in the courseof interactions with electron pairs of the second compound and/or withthe matrix material. As a result of the overlapping of the orbitals, anelectron donor-electron acceptor complex may be generated, in which caseholes (defect electrons) migrate. In the case of hole transport, anelectron from a HOMO (Highest Occupied Molecular Orbital) fills a hole.The holes are transported via the matrix material, since there arepercolation pathways here. The electron acceptor withdraws an electronentirely or partly from the matrix material and therefore generates ahole in the matrix material. This hole then migrates according to theprocess above. This increases the hole conductivity, the efficiency, andthe lifetime of the optoelectronic component.

Additionally or alternatively, the coordination sites may be easilyaccessible and are not shielded by ligands.

According to one embodiment the first compound comprises a structuralunit 1

and/or a structural unit 2

wherein Cu in the structural unit 1 does not necessarily mean onlycopper, Cu instead standing for a complexed metal which is selected froma group which comprises copper, chromium, molybdenum and bismuth, andcombinations thereof, and Cr in the structural unit 2 does notnecessarily mean only chromium, Cr instead standing for a complexedmetal which is selected from a group which comprises copper, chromium,molybdenum and bismuth, and combinations thereof. In particular, Crstands for a divalent bismuth.

R₁, R₂, R₃ and/or R₄ are identical or nonidentical and are each selectedfrom a group which comprises substituted or unsubstituted hydrocarbonradicals, alkyl radicals, cycloalkyl radicals, heterocycloalkylradicals, aryl radicals, heteroaryl radicals, and combinations thereof.The hydrocarbon radicals or alkyl radicals may be branched, linear orcyclic. The aryl and/or heteroaryl radicals may have one ring or aplurality of rings. The rings may be fused. A “ring” in this contextmeans a cyclic association of atoms which are selected, for example,from a group comprising C, S, N, Si, O, P, and combinations thereof.“Fused” rings in this context means that a plurality of rings have atleast one shared atom. Accordingly, even a spiro compound whose ringsare joined only at one atom may be referred to as fused. In particular,at least two rings share two atoms with one another.

According to at least one embodiment, central metal atoms which compriseCr and/or Mo form a dimeric first compound. Cu as central metal atomforms a tetrameric, hexameric, etc. first compound. In particular,trivalent Bi as central metal atom does not form a first compoundaccording to structural unit 2.

In particular, 2 to 6 rings, more particularly 4 rings, are fused.Alternatively or additionally, the ring or the plurality of rings mayhave a conjugation. “Conjugation” in this context means that the ring orthe plurality of rings has single and double bonds in alternation.

The arrows in the structural units 1 or 2 show possible coordinationsites on the central metal atoms of the first compound.

The structural unit 1 has at least four free coordination sites. Thestructural unit 2 has at least two coordination sites.

Branched, linear or cyclic hydrocarbon radicals may comprise, inparticular, 1-20 carbon atoms, examples being methyl, ethyl or fusedrings, such as decahydronaphthyl or adamantyl, cyclohexyl, or wholly orpartly substituted alkyl radicals. Alternatively or additionally, R₁,R₂, R₃ and/or R₄ may comprise substituted or unsubstituted arylradicals, examples being phenyl, biphenyl, naphthyl, phenanthryl,benzyl, mesityl or heteroaryl radicals, examples being substituted orunsubstituted radicals selected from the following aromatic parentstructures (scheme 1):

According to one embodiment, the first compound is tetrakis-Cu(I)perfluorobenzoate, referred to here and below by the abbreviateddesignation Cu(I)pFBz, or dichromium(II) tetrakistrifluoroacetate. Inprinciple, however, further compounds known per se may also be used asfirst compound.

According to one embodiment, the first compound may be selected from agroup which comprises copper(I) complexes as described, for example, inUS 2011/0 089 408 A1, copper(II) complexes as described, for example, inUS 2011/0 089 408 A1, copper(II) acetylacetonate as described, forexample in DE 10 2010 013 495 A1, metal complexes, such as rhodiumtrifluoroacetate, for example, as described, for example, in DE 10 2007028 237 A1 and DE 10 2007 028 238 A1.

The above-described embodiments of the first compound differ here intheir electron acceptor strength in relation to the matrix material andrelative to an identical concentration of the first compound in thematrix material. The first compound is in particular a copper(I) complexas described, for example, in US 2011/0 089 408 A1, and a rhodiumcomplex, such as rhodium trifluoroacetate, for example, as described,for example, in DE 10 2007 028 237 A1 and DE 10 2007 028 238 A1. Thisconfers a positive influence on the appearance of the optoelectroniccomponent in the switched-off state.

According to one embodiment, the second compound comprises an aromaticand/or heteroaromatic which has at least two functional groups which arecapable of forming a coordinate bond and/or of π-π interaction.

The π-π interaction may be developed in particular between aromaticswith different acceptor strengths of first, second and/or the matrixmaterial.

π-π interactions are forces which occur between π-systems of molecules,examples being π-systems of unsaturated compounds, and which come aboutas a result of their quadrupole moments.

The aromatics and/or heteroaromatics in particular have a ring or aplurality of rings. The aromatics and/or heteroaromatics may inparticular comprise 2 to 6 rings, more particularly 4 rings.Alternatively or additionally, the ring or the plurality of rings isfused.

The functional groups are selected more particularly from a group whichcomprises amine, phosphine, phenol, thiol, cyano, isocyano, cyanato,nitrato, carboxylato, fluorinated carboxylato, acetylacetonate,fluorinated acetylacetonate, carbonyl, amide, imide, thienyl, fluoro,and combinations thereof.

The functional groups may also be electron donors.

According to one embodiment, the functional groups are capable offorming coordinate bonds which are developed to the first compoundand/or to the matrix material.

According to one embodiment, the second compound has hole-conductingproperties. The second compound may conduct holes or positive charges.As a result of this, the conductivity of the organic functional layermay be increased. This results in a lower voltage drop in the organicfunctional layer and hence in a higher efficiency of the optoelectroniccomponent in comparison to an organic functional layer having a lowerconductivity and a greater voltage drop, provided the charge carrierequilibrium remains constant. An additional effect of this is a higherexciton density in the layer which emits radiation, and hence a higherluminous efficiency of the optoelectronic component.

According to one embodiment, the second compound comprises at least oneheteroaromatic which comprises at least one of the aromatic parentstructures from scheme 1. In particular, the functional groups arelinked to at least one aromatic parent structure from scheme 1.

The second compound may additionally have a conjugation; for example,the second compound has alternating single and double bonds.

According to one embodiment, the second compound comprises a structuralunit 3

and/or a structural unit 4

wherein F1, F2, F3, F4, F5, F6, F7, F8, F9 and/or F10 may be identicalor nonidentical, are independent of one another, and are selected from agroup which comprises amine, phosphine, phenol, thiol, cyano, isocyano,cyanato, nitrato, carboxylato, carbonyl, amide, imide, tienyl, fluoro,and combinations thereof. Cyanato is preferred in particular.

Alternatively or additionally, the structural units 3 or 4 may besubstituted on the C atoms. Substituents may be selected from a groupwhich comprises alkyl, aryl, heteroaryl, cycloalkyl, fluoro.

The second compound is selected more particularly from a group whichcomprisesdipyrazino[2,3-ƒ:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile(used here with the abbreviated designation HAT-CN),7,7,8,8-tetracyanoquionodimethane (used here with the abbreviateddesignation TCQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane(used here with the abbreviated designation FCQ),2,3-di(N-phthalimido)-5,6-dicyano-1,4-benzoquinone (used here with theabbreviated designation PBQ),pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile and thefluorinated or unfluorinated derivatives thereof, andtetracyanonaphthoquinodimethane and the fluorinated or unfluorinatedderivatives thereof. The formulae of HAT-CN, TCQ, FCQ and PBQ are shownbelow. The arrows on the formulae show possible coordination sites whichare capable of coordinating, for example, to the first compound and/orto the matrix material.

According to one embodiment, the second compound has a π-electron systemwhich comprises at least one ring, as for example, 1 to 6 rings. As aresult, electrons of the first compound and/or second compound and/orholes may be localized in the matrix material. This results in a higherconductivity of the organic functional layer and therefore leads to ahigher luminous efficiency of the optoelectronic component.

In one embodiment of the optoelectronic component, the metal complex ofthe first compound coordinates to one of the functional groups or to aplurality of the functional groups of the second compound. Thecoordination of the second compound to the central metal atom of thefirst compound may be via the functional groups of the second compoundor via an atom, N, P, S or O for example, in the aromatic system of thesecond compound. During or after the coordination of the first compoundto the second compound, there is preferably no elimination of the metalcomplex ligands treated beforehand, and therefore there is no ligandexchange.

According to one embodiment, the first compound forms a plurality ofcoordinate bonds with the second compound in such a way as to produce achainlike structure and/or a netlike structure.

It is also possible for additional compounds to be incorporated into thematrix material, these compounds forming a chainlike and/or netlikestructure—a three-dimensional structure, for example—by interaction withthe first compound, the second compound and/or the matrix material.

According to one embodiment, the first compound, as well as having a“central metal atom” structural element M, has at least one “freecoordination site” structural element KS_(n) (index n here denotes thenumber of coordination sites). The second compound has an “aromaticsand/or heteroaromatics” structural element A and at least one“functional group” structural element FG_(m) (index m here denotes thenumber of functional groups). A “structural element” in this contextrefers to a characteristic region of the structural formula. Forexample, the “functional group” structural element FG_(n) comprises allabove-treated functional groups of the second compound. The “centralmetal atom” structural element M comprises the above-treated centralmetal atoms of the first compound. The “free coordination site”structural element KS_(n) comprises the above-treated free coordinationsites of the first compound. The “aromatics and/or heteroaromatics”structural element A comprises the above-treated aromatics and/orheteroaromatics of the second compound. At least one “free coordinationsite” structural element, for example, KS₁, is capable of interactingwith the “functional group” structural element, for example, FG₁ of thesecond compound. This may be generated, for example, by formation of atleast one coordinate bond. As a result it is possible for a chainlikestructure and/or a netlike structure to form (see schematic diagrambelow).

Here and in this context:

M: denotes a “central metal atom” structural element of the firstcompound

KS_(n): denotes an “nth free coordination site” structural element ofthe first compound,

KS₁: denotes a “first free coordination site” structural element of thefirst compound,

KS₂: denotes a “second free coordination site” structural element of thefirst compound,

A: denotes an “aromatics and/or heteroaromatics” structural element ofthe second compound,

FG_(m): denotes an “mth functional group” structural element of thesecond compound,

FG₁: denotes a “first functional group” structural element of the secondcompound,

FG₂: denotes a “second functional group” structural element of thesecond compound, and

W: denotes interactions between “first free coordination site”structural element of the first compound and “first functional group”structural element of the second compound.

According to one embodiment, the first compound and/or second compoundmay be used as a p-dopant. “p-Dopant” in this context means that thedopant is capable of receiving electrons of the matrix material and sogenerating holes in the matrix material.

According to one embodiment, the organic functional layer is a holetransport layer. The addition of a first compound to a second compoundin a matrix material of the hole transport layer results in an improvedhole transport capacity as compared with the matrix material whichcomprises no first and second compounds. This improved hole transportcan be explained by the transfer of the holes or of the positive chargeof the molecules of the matrix material that are able to interact withthe first or second compound.

The following are shown below by way of example:

scheme 2: interaction of the first compound, exemplified by Cu(I)pFBz,with the second compound, exemplified by HAT-CN;

scheme 3: interaction of the first compound, exemplified by Cu(I)pFBz,with the second compound, exemplified by HAT-CN, and interaction of thefirst compound, exemplified by Cu(I)pFBz, with the matrix material,exemplified by N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)benzidene(NPD); and

scheme 4: interaction of the first compound, exemplified by Cu(I)pFBz,with the second compound, exemplified by HAT-CN, and interaction of thesecond compound, exemplified by HAT-CN, with the matrix material,exemplified by NPD. The interactions are not limited to the interactionsshown in schemes 1 to 4 or other interactions of compounds described inthe working examples. Instead, another working example of the firstcompound, second compound and/or matrix material may also be utilized.In addition it is possible for first compound, second compound and/ormatrix material to interact via at least one π-π interaction between twoaromatics with different acceptor strengths, as is shown, for example,in DE 10 2007 028 238 A1 and/or in Sevryugina et al., Inorg. Chem. 2007,46, 7870-7879.

According to one embodiment, not all molecules of the matrix materialinteract with the molecules of the first compound and/or secondcompound.

The matrix material, the hole transport layer, for example, may beselected from a group which comprises one or more compounds of thefollowing groups: NPB(N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)benzidine, β-NPB(N,N′-bis(naphthalen-2-yl)-N,N′-bis(phenyl)benzidine), TPD(N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine),N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-2,2-dimethylbenzidine,spiro-TPD(N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-spirobifluorene),spiro-NPB(N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-spirobifluorene),DMFL-TPD(N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-dimethylfluorene,DMFL-NPB(N,N′-bis(naphthalen-1-yl)-N,N′-bis(phenyl)-9,9-dimethylfluorene),DPFL-TPD(N,N′-bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9-diphenylfluorene),DPFL-NPB (N,N′-bis(naphth-1-yl)-N,N′-bis(phenyl)-9,9-diphenylfluorene),Sp-TAD (2,2′,7,7′-tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene),TAPC (di[4-(N,N-ditolylamino)phenyl]cyclohexane), spiro-TTB(2,2′,7,7′-tetra(N,N-ditolyl)aminospirobifluorene), BPAPF(9,9-bis[4-(N,N-bisphenyl-4-yl-amino)phenyl]-9H-fluorene), spiro-2NPB(2,2′,7,7′-tetrakis[N-naphthyl(phenyl)amino]-9,9-spirobifluorene),spiro-5(2,7-bis[N,N-bis(9,9-spirobifluoren-2-yl)amino]-9,9-spirobifluorene),2,2′-spiro-DBP(2,2′-bis[N,N-bis(biphenyl-4-yl)amino]-9,9-spirobifluorene), PAPB(N,N′-bis(phenanthren-9-yl)-N,N′-bis(phenyl)benzidine), TNB(N,N,N′,N′-tetranaphthalen-2-yl-benzidine), spiro-BPA(2,2′-bis(N,N-diphenylamino)-9,9-spirobifluorene), NPAPF(9,9-bis[4-(N,N-bisnaphth-2-yl-amino)phenyl]-9H-fluorene), NPBAPF(9,9-bis[4-(N,N′-bisnaphth-2-yl-N,N′-bisphenylamino)phenyl]-9H-fluorene),TiOPC (titanium oxide phthalocyanine), CuPC (copper phthalocyanine),F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane), m-MTDATA(4,4′,4″-tris(N-3-methylphenyl-N-phenylamino)triphenylamine), 2T-NATA(4,4′,4″-tris(N-(naphthalen-2-yl)-N-phenylamino)triphenylamine), 1T-NATA(4,4′,4″-tris(N-(naphthalen-1-yl)-N-phenylamino)triphenylamine), NATA(4,4′,4″-tris(N,N-diphenylamino)triphenylamine), PPDN(pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile), MeO-TPD(N,N,N′,N′-tetrakis(4-methoxy-phenyl)benzidine), MeO-spiro-TPD(2,7-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobifluorene),2,2′-MeO-spiro-TPD(2,2′-bis[N,N-bis(4-methoxyphenyl)amino]-9,9-spirobifluorene), β-NPP(N,N′-di(naphthalen-2-yl)-N,N′-diphenylbenzene-1,4-diamine), NTNPB(N,N′-diphenyl-N,N′-di-[4-(N,N-ditolylamino)phenyl]benzidine and NPNPB(N,N′-diphenyl-N,N′-di-[4-(N,N-diphenylamino)phenyl]benzidine). Thelisting is by no means limited, however. Any matrix material whichcommonly transports holes is suitable as a constituent of the organicfunctional layer.

According to one embodiment, the fraction of the matrix material in theorganic functional layer is more than 50%, preferably more than 80%, andmore preferably more than 90%, as for example, 95%.

In a further embodiment, the organic functional layer is anelectron-blocking layer.

Further specified is an organic functional layer which comprises amatrix material, a first compound, and a second compound, the firstcompound forming an electron donor-electron acceptor complex with thesecond compound via at least one coordinate bond, and the first compoundand/or the second compound interacting, as electron acceptor, with thematrix material, and the interaction in the electron donor-electronacceptor complex generating conductivity in the organic functionallayer.

For the organic functional layer, the matrix material, the firstcompound and/or the second compound, the definitions and observationswhich apply are the same as those specified above in the description foran optoelectronic component.

According to one embodiment, the conductivity of the organic functionallayer is greater than a sum of a first conductivity, generated by soleinteraction of the first compound with the matrix material, and of asecond conductivity, generated by sole interaction of the secondcompound with the matrix material.

According to one embodiment, the organic functional layer is aconstituent of an organic light-emitting diode, of a transistor, a fieldeffect transistor, for example, of a solar cell or of a photodetector.

Further specified is a method for producing an optoelectronic component,the method comprising the following steps:

A) providing a substrate,

B) applying a first electrode,

C) depositing at least one organic functional layer or a plurality oforganic functional layers on the substrate,

D) applying a second electrode,

the depositing of the organic functional layer taking place bysimultaneous vaporization from different sources of a first compound, ofa second compound, and of a matrix material.

The deposition of the organic functional layer by simultaneousvaporization from different sources of a first compound, of a secondcompound, and of a matrix material causes a higher conductivity on thepart of the organic functional layer. Particularly when using an organicfunctional layer having a thickness of 5 nm to 600 nm, preferably 100 to400 nm, to reduce the susceptibility to an electrical short-circuit inthe optoelectronic component, in extensive OLEDs, for example, thevertical voltage drop across the organic functional layer can be reducedfurther, thereby boosting efficiency, including luminous efficiency, ofthe optoelectronic component. Additionally, the lateral currentdistribution of the optoelectronic component can be improved if theconductivity of the organic functional layer is in the order ofmagnitude of conductivity of the first electrode and/or secondelectrode, such as of indium tin oxide, i.e., tin oxide-doped indiumoxide (no), for example.

Alternatively or additionally, in method step D, at least the first andsecond compounds may be mixed prior to vaporization, with the depositingof the organic functional layer taking place by simultaneousvaporization from a source of the first and second compounds and fromanother source of the matrix material.

For the method for producing an optoelectronic component, thedefinitions and observations which apply are the same as those specifiedabove in the description for an optoelectronic component.

According to one embodiment, the number of coordinate bonds between thefirst organic compound and the second organic compound and/or betweenthe first organic compound and the matrix material and/or between thesecond organic compound and the matrix material may be controlled byconcentration change during vaporization.

FIG. 1 shows a schematic side view of an optoelectronic component, usingthe working example of an organic light-emitting diode (OLED). The OLEDcomprises a substrate 1, which is located right at the bottom and maybe, for example, transparent and may be made of glass. Arranged on thesubstrate 1 is a first electrode 2, which may be formed as a layer, andmay be, for example, a transparent conductive oxide such as, forexample, zinc oxide, tin oxide, cadmium oxide, titanium oxide, indiumoxide or indium tin oxide (ITO). Located above this electrode layer 2 isa hole injection layer 3, arranged above which in turn is the holetransport layer 4. Located thereon is a layer which emits radiation andwhich may have, for example, a plurality of individual layers. On thelayer 5 which emits radiation there is the hole-blocking layer 6, onwhich the electron transport layer 7 and, lastly, the electron injectionlayer 8, with adjacent second electrode 9, may be arranged. The secondelectrode 9 may be, for example, a metal electrode or a furthertransparent electrode, made from one of the aforementioned transparentconductive oxides, for example. The organic functional layer of theinvention is, for example, the hole injection layer, hole transportlayer, hole blocking layer, or layer which emits radiation.

If a voltage is applied between the first electrode 2 and the secondelectrode 9, current flows through the optoelectronic component. In thatcase, one electrode, the cathode, injects electrons into the electroninjection layer 8, and the other electrode, the anode, injects what arecalled holes. In the layer 5 which emits radiation, the holes andelectrons recombine, forming electron-hole pairs, known as excitons,which are capable of emitting electromagnetic radiation.

Alternatively, an optoelectronic component (not shown here) is formed asan OLED with substrate 1, first electrode 2, organic functional layerand second electrode 9.

An alternative possibility is an arrangement of an optoelectroniccomponent (not shown here) in the form of an OLED composed of substrate1, first electrode 2, hole injection layer 3, electron transport layer5, and second electrode 9.

Alternatively or additionally, the first and second compounds in thematrix material are formed as a film or as a casting, and are arrangedor applied to or over the first electrode (not shown here).

Alternatively it is possible to form the hole injection layer 3, thehole transport layer 4 or the layer 5 which emits radiation as anorganic functional layer, with the organic functional layer comprisingthe first compound and second compound in a matrix material.

The organic functional layer in accordance with the present inventionhere may be any layer in which holes are transported. The organicfunctional layer in accordance with the invention preferably comprisesthe hole injection layer 3 or hole transport layer 4. The organicfunctional layer may also, however, be the layer 5 which emitsradiation, for example, in such a way, for example, that a furthermaterial, emitting radiation, is vaporized with the first compound andwith the second compound. Alternatively, however, the material whichemits radiation may also be incorporated otherwise into the layer 5which emits radiation. As a result of the improved hole transportcapacity, a greater number of holes and electrons are able to recombine,thus forming more excitons (electron-hole pairs). This results in anincrease in the exciton density in the layer 5 which emits radiation,thereby increasing the luminance and efficiency of the optoelectroniccomponent.

Here and below, the following abbreviated designations are used forcomparative examples of first compound or second compound in the matrixmaterial:

V1: comparative example of a first compound Cu(I)pFBz in the matrixmaterial HTM-014 by Merck

V8: comparative example of a second compound HAT-CN in the matrixmaterial HTM-014, and

A1: working example of a first compound Cu(I)pFBz with a solid fractionof 5% and a second compound HAT-CN with a variable fraction in thematrix material HTM-014.

FIG. 2 shows the specific conductivity K in siemens per meter (S×m⁻¹) ofcomparative examples V1 and V8, and also of working example A1, as afunction of the concentration c, expressed as a volume percentage, ofthe first compound Cu(I)pFBz or of the second compound HAT-CN. In thiscase, an organic test structure was used for the conductivitymeasurement in accordance with FIG. 3. In FIG. 3, d denotes thickness ofthe organic test structure, L length of the organic test structure, Swidth of the organic test structure, K1 first contact, and K2 secondcontact. Applied between the contacts K1 and K2 is a voltage, therebyforming a homogeneous electrical field F in the semiconductor. Thespecific conductivity K then results according to the followingequation:

$K = {\frac{j}{F} = {\frac{j \cdot S}{U} = \frac{I \cdot S}{U \cdot L \cdot d}}}$wherein j is current density and U is voltage.

By simultaneous thermal vaporization from different sources, therespective matrix material, the first compound and the second compoundwere deposited, as an organic functional layer with an overall thicknessof 120 nm, on an ITO (indium tin oxide=tin oxide-doped indium oxide)electrode. The specific conductivity K was calculated from thecurrent-voltage characteristic curve, and has been representedgraphically in FIG. 2 and FIG. 4.

The matrix material exhibits a relatively poor specific conductivity, K,of less than 10⁻⁶ S×m⁻¹ (not shown here). By vaporization of the firstcompound or second compound in the matrix material, however, it ispossible to achieve a specific conductivity K of significantly greaterthan 10⁻⁶ S×m⁻¹. The first compound Cu(I)pFBz in the matrix materialHTM-014 (V1) generates a higher specific conductivity K than the secondcompound HAT-CN in the matrix material HTM-014 (V8). For an identicalconcentration, the specific conductivity K for comparative example V1,for Cu(I)pFBz in HTM-014, is higher by two orders of magnitude incomparison to V8, comprising HAT-CN in HTM-014. With increasingconcentration of the first compound Cu(I)pFBz or second compound HAT-CN,an increase is observed in the specific conductivity K. This resultsfrom interactions of the first compound Cu(I)pFBz or second compoundHAT-CN with the respective matrix material. As a result, a high holemobility and charge transfer are made possible, and the luminousefficiency of the optoelectronic component is improved.

Here and below, the following abbreviated designations are used forworking examples and comparative examples of first compound and/orsecond compound in the matrix material:

V9: comparative example of a second compound HAT-CN with a fraction of10% in the matrix material HTM-014,

V10: comparative example of a first compound Cu(I)pFBz with a fractionof 5% in the matrix material HTM-014,

A1: working example of a first compound Cu(I)pFBz with a fraction of 5%and of a second compound HAT-CN with a fraction of 10% in the matrixmaterial HTM-014, and

V11: comparative example of a first compound Cu(I)pFBz with a fractionof 5% in the matrix material HTM-014. “Fraction” in this context denotesthe volume percent of the first compound or of the second compoundrelative to the matrix material.

FIG. 4 shows the specific conductivity K in siemens per meter (S×m⁻¹) ofV9, V10, A1 and V11. The specific conductivity K of V9 is in the orderof magnitude of 10⁻⁵ S/m, whereas the specific conductivity K of V10 andV11 is higher by one order of magnitude (K=10⁻⁴ S/m). Surprisingly, thespecific conductivity K of A1 is increased further by almost one orderof magnitude (approximately 10⁻³ S/m). The specific conductivity K ofthe organic functional layer is increased significantly by the additionof the first compound and of the second compound in the matrix material,in contrast to the specific conductivity K, which is generated by soleinteraction of the first compound with the matrix material (V10 or V11),and to the specific conductivity K which is generated by soleinteraction of the second compound with the matrix material (V9). Thespecific conductivity K of A1 comes about through an advantageousnetwork of the first compound Cu(I)pFBz and of the second compoundHAT-CN in the matrix material HTM-014. In the case of the vaporizationof Cu(I)pFBz and HAT-CN, there is no cross-contamination of materials inthe sources. This is shown in FIG. 4 by the virtually identical specificconductivities K of V10 and V11, which were produced before and afterA1, respectively.

Synthesis of copper(I) pentafluorobenzoate

Cu₂O (0.451 g, 3.15 mmol) is admixed with 2 ml of (CF₃CO)₂O, followed by30 ml of benzene. The mixture is heated under reflux overnight, giving ablue solution and a little unreacted starting material. This suspensionis filtered using Celiter, in order to remove Cu₂O. The blue solution isthen evaporated to dryness, giving a very pale blue solid. The desiredproduct is obtained by operating under reduced pressure at 60° C. to 70°C. for ten to 15 hours. The yield is 64%. The crystalline material canbe obtained by sublimation of the crude solid at 110° C. to 120° C.

The reaction product (0.797 g, 1.1 mmol) is kept with pentafluorinatedbenzoic acid (0.945 g, 6.76 mmol) in a Schlenk flask in a glovebox, with55 ml of benzene being added to the mixture. A homogeneous light-bluesolution is heated under reflux overnight and then evaporated todryness, giving a pale blue solid. Operation takes place under reducedpressure at 90° C. to 100° C. for several days, in order to remove theexcess of unreacted benzoic acid. A colorless solid stable in air isobtained by sublimation deposition of the crude powder at 220° C. aftera week. The yield of copper(I) pentafluorobenzoate is 65%.

Production of the Organic Functional Layer

The first compound (for example, Cu(I)pFBz), second compound (forexample, HAT-CN) and the matrix material (for example, HMT-014), each indifferent sources, are heated thermally to their respective sublimationpoints, and these compounds are vaporized simultaneously. In thisoperation, the first compound, the second compound and the matrixmaterial are applied as an organic functional layer to a firstelectrode, ITO, for example.

Production of an Optoelectronic Component

The organic functional layer produced can be deposited on a providedsubstrate, glass, for example, on which a first electrode has beenapplied, with a second electrode being applied thereto.

The invention is not restricted by the description using the workingexamples or specified combinations of features. Instead, the inventionalso encompasses individual new features as such and also anycombination of specified features, including in particular anycombination of features in the claims, even if that feature or thatcombination is not itself explicitly indicated in the claims or workingexamples.

The invention claimed is:
 1. An optoelectronic component comprising: asubstrate; a first electrode; a second electrode; and an organicfunctional layer arranged between the first electrode and the secondelectrode, the organic functional layer comprising a matrix material, afirst compound, and a second compound, wherein the first compoundinteracts with the second compound, wherein the first compound and/orthe second compound interacts with the matrix material, wherein theinteractions generate conductivity in the organic functional layer,wherein at least one coordinate bond is formed by the first compoundwith the second compound and at least one coordinate bond is formed bythe first compound with the matrix material, or at least one coordinatebond is formed by the first compound with the second compound and atleast one coordinate bond is formed by the second compound with thematrix material, wherein the first compound comprises a compoundselected from the group consisting of the following structural units orformula:

wherein, in formulae I and II, R₁, R_(1′), R_(2a), R_(2a′), R_(2b),R_(2b′), R_(2c), R_(2c′), R_(2d), and R_(2d′), independently of oneanother and each is selected from the group consisting of unbranchedunsubstituted and substituted alkyl radicals, branched unsubstituted andsubstituted alkyl radicals, fused unsubstituted and substituted alkylradicals, cyclic unsubstituted and substituted alkyl radicals,substituted and unsubstituted aromatics, and substituted andunsubstituted heteroaromatics, wherein, in formulae III, R₁, R₂, R₃ andR₄ are identical or unidentical and each is selected from the groupconsisting of substituted or unsubstituted alkyl radicals, substitutedor unsubstituted cycloalkyl radicals, substituted or unsubstitutedheterocycloalkyl radicals, substituted or unsubstituted aryl radicals,substituted or unsubstituted heteroaryl radicals, and combinationsthereof, wherein, in formulae III, X is chromium, molybdenum, bismuth orCu and Cr, and wherein the second compound comprises a compound selectedfrom the group consisting ofdipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile,7,7,8,8-tetracyanoquiono-dimethane,2,3-di(N-phthalimido)-5,6-dicyano-1,4-benzoquinone,pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile and fluorinatedor unfluorinated derivatives thereof, andtetracyanonaphthoquinodimethane and fluorinated or unfluorinatedderivatives thereof.
 2. The optoelectronic component according to claim1, wherein the organic functional layer comprises a layer selected fromthe group consisting of a hole transport layer, a hole injection layer,and a hole blocking layer.
 3. The optoelectronic component according toclaim 1, wherein the conductivity of the organic functional layer isgreater than a sum of a first conductivity, generated by soleinteraction of the first compound with the matrix material, and of asecond conductivity, generated by sole interaction of the secondcompound with the matrix material.
 4. The optoelectronic componentaccording to claim 1, wherein the first compound comprises an electronacceptor in relation to the matrix material and/or an electron acceptorin relation to the second compound.
 5. The optoelectronic componentaccording to claim 1, wherein the second compound comprises an electronacceptor in relation to the matrix material and/or an electron donor inrelation to the first compound.
 6. The optoelectronic componentaccording to claim 1, wherein a third compound is generated bycomplexing of first and second compounds in a gas phase, the thirdcompound produced by simultaneous vaporization from different sources ofthe first compound, of the second compound and of the matrix material.7. The optoelectronic component according to claim 1, wherein the secondcompound comprises an aromatic and/or heteroaromatic that has at leasttwo functional groups that are capable of forming a coordinate bondand/or of π-π interaction.
 8. The optoelectronic component according toclaim 7, wherein the functional groups comprises functional groupsselected from the group consisting of amine, phosphine, phenol, thiol,cyano, isocyano, cyanato, nitrato, carboxylato, fluorinated carboxylato,acetylacetonate, fluorinated acetylacetonate, carbonal, amide, imide,thienyl, fluoro, and combinations thereof.
 9. The optoelectroniccomponent according to claim 1, wherein the first compound forms atleast one coordinate bond with the second compound, to give a chainlikestructure and/or a netlike structure.
 10. The optoelectronic componentaccording to claim 1, wherein at least one coordinate bond is formed bythe first compound with the second compound and at least one coordinatebond is formed by the first compound with the matrix material.
 11. Theoptoelectronic component according to claim 1, wherein at least onecoordinate bond is formed by the first compound with the second compoundand at least one coordinate bond is formed by the second compound withthe matrix material.
 12. An organic functional layer comprising: amatrix material; a first compound; and a second compound, wherein atleast one coordinate bond is formed by the first compound with thesecond compound and at least one coordinate bond is formed by the firstcompound with the matrix material or wherein at least one coordinatebond is formed by the first compound with the second compound and atleast one coordinate bond is formed by the second compound with thematrix material, wherein the first compound forms an electrondonor-electron acceptor complex with the second compound via at leastone coordinate bond, wherein the first compound and/or the secondcompound, as electron acceptor or as electron acceptors, interact withthe matrix material, wherein the interactions and the electrondonor-electron acceptor complex generate conductivity in the organicfunctional layer, wherein the first compound comprises a compoundselected from the group consisting of the following structural units orformula:

wherein, in formulae I and II, R₁, R_(1′), R_(2a), R_(2a′), R_(2b),R_(2b′), R_(2c), R_(2c′), R_(2d) and R_(2d′) independently of oneanother and each is selected from the group consisting of unbranchedunsubstituted and substituted alkyl radicals, branched unsubstituted andsubstituted alkyl radicals, fused unsubstituted and substituted alkylradicals, cyclic unsubstituted and substituted alkyl radicals,substituted and unsubstituted aromatics, and substituted andunsubstituted heteroaromatics, wherein, in formulae III, R₁, R₂, R₃ andR₄ are identical or unidentical and each is selected from the groupconsisting of substituted or unsubstituted alkyl radicals, substitutedor unsubstituted cycloalkyl radicals, substituted or unsubstitutedheterocycloalkyl radicals, substituted or unsubstituted aryl radicals,substituted or unsubstituted heteroaryl radicals, and combinationsthereof, wherein, in formulae III, X is chromium, molybdenum, bismuth orCu and Cr, and wherein the second compound comprises a compound selectedfrom the group consisting ofdipyrazino[2,3f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile,7,7,8,8-tetracyanoquiono-dimethane,2,3-di(N-phthalimido)-5,6-dicyano-1,4-benzoquinone,pyrazino[2,3-f][1,10]phen-anthroline-2,3-dicarbonitrile and fluorinatedor unfluorinated derivatives thereof, andtetracyanonaphthoquinodimethane and fluorinated or unfluorinatedderivatives thereof.
 13. The organic functional layer according to claim12, wherein the conductivity of the organic functional layer is greaterthan a sum of a first conductivity, generated by sole interaction of thefirst compound with the matrix material, and of a second conductivity,generated by sole interaction of the second compound with the matrixmaterial.
 14. An optoelectronic component comprising: a substrate; afirst electrode; a second electrode; and an organic functional layerarranged between the first electrode and the second electrode, theorganic functional layer comprising a matrix material, a first compound,and a second compound, wherein the first compound interacts with thesecond compound, wherein the first compound and/or the second compoundinteracts with the matrix material, wherein the interactions generateconductivity in the organic functional layer, wherein at least onecoordinate bond is formed by the first compound with the second compoundand at least one coordinate bond is formed by the first compound withthe matrix material, or at least one coordinate bond is formed by thefirst compound with the second compound and at least one coordinate bondis formed by the second compound with the matrix material, wherein thefirst compound comprises a compound selected from the group consistingof the following structural units or formula:

wherein, in formulae I and II, R₁, R_(1′), R_(2a), R_(2a′), R_(2b),R_(2b′), R_(2c), R_(2c′), R_(2d), and R_(2d′), independently of oneanother and each is selected from the group consisting of unbranchedunsubstituted and substituted alkyl radicals, branched unsubstituted andsubstituted alkyl radicals, fused unsubstituted and substituted alkylradicals, cyclic unsubstituted and substituted alkyl radicals,substituted and unsubstituted aromatics, and substituted andunsubstituted heteroaromatics, wherein the second compound comprises acompound selected from the group consisting ofdipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile,2,3-di(N-phthalimido)-5,6-dicyano-1,4-benzoquinone, and fluorinated orunfluorinated derivatives thereof, and tetracyanonaphthoquinodimethaneand fluorinated or unfluorinated derivatives thereof.